I WAS LISTENING recently to a Bob Dylan song, From a Buick 6. One of the song’s lines is, “I need a dump truck, baby, to unload my head.” That’s how I sometimes feel about the churning in my own mind concerning retirement.
I turned 67 this year. This is probably one of the most critical periods for me as a retiree. There are things in my life I need to sort out,

RAISE YOUR WALLET if you think taxes won’t be going up.
Is there much doubt that the federal government will seek additional revenue, given its ballooning debt and future spending on Social Security, Medicare and other federal programs? If so, should retirement savers really be deferring taxes—or, instead, should we be taking advantage of tax-free retirement savings?
The IRA was first introduced in 1974. At that time, there was a 38% tax rate on individual incomes of more than $20,000,

IN THE SUMMER of 1789, George Washington got into a dispute with his Postmaster General—a fellow named Ebenezer Hazard—and removed him from office.
Looking for a new profession, Hazard decided to start an insurance company. He called his new firm the Insurance Company of North America and specialized in providing life insurance to ship captains. The business was a perfect fit for the times and quickly prospered. Still, I’m sure that even Hazard would be surprised to see his company still in business more than two centuries later.

IS IT TIME TO STOP messing around with our portfolios—and go for radical simplicity? I’ve been asking myself that question in recent months, as I eye the growing list of funds that offer broadly diversified “one-stop shopping” portfolios built solely with low-cost index funds.
Take Vanguard Target Retirement 2050 Fund, which invests its assets in four Vanguard index funds and is geared toward those retiring in 2050 or thereabouts. The 2050 fund has a $1,000 investment minimum and charges just 0.15% a year,

“THERE ARE TWO kinds of people in the world…” There are Republicans and Democrats. Right-brained and left-brained. Yankees fans and Red Sox fans. And, of course, Starbucks people and Dunkin’ Donuts people.
In Boston, where Dunkin’ was founded and where I live, this is a particularly strong theme. Dunkin’ people and Starbucks people see themselves as very different. Starbucks aficionados see it as a higher-quality experience and don’t mind paying for it. Meanwhile, Dunkin’ fans are proud of their frugality and think that the people over at Starbucks are overpaying.

I HAVE A PENSION, a 401(k) plan and other investments, and no debt. I worked more than 50 years to accumulate what I have. Still, I realize I am fortunate.
That brings me to a list of advice for seniors that’s now making the rounds on the internet. I found it fascinating—and disturbing. The list is presented for “those of us who are between 65 and death, i.e. old.” Many people who have read the list buy into the philosophy behind it.

IN HER BESTSELLING book Thinking in Bets, retired poker champion Annie Duke stresses an important point: As kids in school, it was regarded as a failure if we ever answered a question, “I don’t know.” But in the world outside the classroom, the only honest answer to many questions is, “I don’t know” or “I’m not sure.” This isn’t due to ignorance. Rather, it’s because, in many cases, the precise right answer simply isn’t knowable.

YOU MAY BE SAVING and investing for retirement. But what you’re really doing is buying future income. How much income? That brings us to a little number crunching, which I hope will illuminate five key financial ideas.
Let’s start with the numbers. Imagine stocks notch 6% a year, but inflation steals two percentage points of that gain, so you collect an after-inflation annual return of 4%. If you socked away $1,000, what would it be worth in retirement?

THE TAX LAW RELIEVES most Social Security recipients of income taxes on their monthly checks. But it requires middle- and upper-income households to count up to 85% of their benefits as reportable income. Sound punishing? It can be especially punishing for couples who are cutting the knot—but they may live happily ever after.
Taxes on Social Security benefits are triggered when recipients’ MAGI exceeds specified amounts. MAGI is an acronym for modified adjusted gross income (and not the term for the three wise men who bore gifts to the infant Jesus).

I FEEL FORTUNATE there weren’t any iPhones or iPads when our son was a toddler. I’ve recently seen two-year-olds mesmerized by the magic of a smartphone. The kids can whiz around a screen like they were born with one in their diaper pocket. It scares me to think how we would have managed these “toys” if they existed in the 1990s.
But they didn’t. From our perspective, Saturday morning cartoons were the biggest threat to our child’s financial development.

MY FATHER WAS AGE 19 and my mother was 11 when the Great Depression started. They were married in 1942 and I was born in late 1943. Their view of money matters was surely tempered by their life experience.
They had no investments to speak of and always kept what little money they had in a checking account. They would never borrow and didn’t know what a credit card was.
Many years ago, I convinced my mother to buy 75 shares of the company I worked for—a large utility.

MUCH PERSONAL finance literature, including most of what I write, focuses on how to handle money—how much to save, which investments to buy, and so forth. But what if you have a more fundamental question: How do I earn more in the first place?
To help answer that question, I have five new summer reading recommendations. Each of these books offers strategies to help you increase your productivity—and your happiness—on the job. That, in turn,

YOU WILL RETIRE ONE day—and, if you want to spend your final decades in even moderate comfort, it won’t be cheap. Not too concerned about saving for retirement right now? Here are five uncomfortable realities:
1. You’ll almost certainly live to retirement age. Sure, you could go under a bus before then. But that isn’t something you should bank on: If you’re age 20 today, there’s an 85% chance you will live to 65,

AS I CHILD, I REMEMBER reading a series of “choose your own ending” adventure books. These novels allowed the reader, at different junctures, to choose how they wanted the main character in the book to proceed. I always enjoyed rereading these books, creating a different story each time I progressed through the pages.
At this point in my life, I’m beginning to feel like my eventual retirement is a bit of a “choose your own ending” adventure.

WHO’S YOUR WORST financial enemy? Got a mirror? For millions of American workers, their employee benefits play a significant role in their financial life—and yet this noncash portion of their compensation is often undervalued, overlooked and misused.
I designed and managed employee benefits for nearly 50 years. During those years, I tried every form of communication I could think of to get employees to pay attention to their benefits. I retired with a sense of failure.